#------------------------------------------------------------------------------
#$Date: 2020-10-06 09:07:57 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257237 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/70/7127070.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7127070
loop_
_publ_author_name
'Liang, Hao'
'He, Xiaobo'
'Zhang, Yaqi'
'Chen, Bin'
'Ouyang, Jia-Sheng'
'Li, Yongsu'
'Pan, Bendu'
'Subba Reddy, Chitreddy V.'
'Chan, Wesley Ting Kwok'
'Qiu, Liqin'
_publ_section_title
;
 Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with
 alkynes.
;
_journal_issue                   77
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11429
_journal_page_last               11432
_journal_paper_doi               10.1039/d0cc04373g
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C19 H15 Br Cl N O4'
_chemical_formula_sum            'C19 H15 Br Cl N O4'
_chemical_formula_weight         436.68
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-06-04 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.7484(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4479(6)
_cell_length_b                   10.9895(5)
_cell_length_c                   14.0720(7)
_cell_measurement_reflns_used    9222
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.51
_cell_volume                     1861.57(15)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Photon-100 CMOS area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            87525
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_T_max  0.5994
_exptl_absorpt_correction_T_min  0.3951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SAINT ver 8.34A; BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0200(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0779P)²+0.9294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                3376
_reflns_number_total             4294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc04373g2.cif
_cod_data_source_block           QLQ1802
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7127070.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7127070
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35973(16) 0.44590(19) 0.15754(15) 0.0804(6) Uani 0.60 1 d P A 1
Cl1' Cl 0.3608(6) 0.4245(6) 0.1640(6) 0.0622(13) Uani 0.40 1 d P A 2
C1 C 0.5102(2) 0.4676(3) 0.1730(2) 0.0561(6) Uani 1 1 d . . .
C2 C 0.5577(3) 0.4179(3) 0.1027(2) 0.0729(9) Uani 1 1 d . A .
H2A H 0.5150 0.3717 0.0515 0.087 Uiso 1 1 calc R . .
C3 C 0.6684(3) 0.4377(3) 0.1094(3) 0.0772(10) Uani 1 1 d . . .
H3A H 0.7003 0.4063 0.0617 0.093 Uiso 1 1 calc R A .
C4 C 0.7321(3) 0.5035(3) 0.1862(3) 0.0730(9) Uani 1 1 d . A .
H4A H 0.8075 0.5150 0.1920 0.088 Uiso 1 1 calc R . .
C5 C 0.6824(2) 0.5521(2) 0.2543(2) 0.0607(7) Uani 1 1 d . . .
Cl1 Cl 0.76587(17) 0.6404(2) 0.3520(3) 0.0774(9) Uani 0.60 1 d P A 1
Br1' Br 0.7683(3) 0.6384(4) 0.3539(4) 0.1634(16) Uani 0.40 1 d P A 2
C6 C 0.5700(2) 0.5374(2) 0.25035(19) 0.0486(6) Uani 1 1 d . A .
C7 C 0.5218(2) 0.5912(2) 0.32711(19) 0.0476(5) Uani 1 1 d . . .
H7A H 0.5124 0.5407 0.3774 0.057 Uiso 1 1 calc R A .
C8 C 0.49124(17) 0.7066(2) 0.32861(16) 0.0390(5) Uani 1 1 d . A .
C9 C 0.48713(18) 0.8043(2) 0.25748(16) 0.0409(5) Uani 1 1 d . . .
C10 C 0.5173(2) 0.8091(3) 0.16881(19) 0.0555(6) Uani 1 1 d . A .
H10A H 0.5468 0.7411 0.1452 0.067 Uiso 1 1 calc R . .
C11 C 0.5025(3) 0.9169(3) 0.1166(2) 0.0698(8) Uani 1 1 d . . .
H11A H 0.5225 0.9217 0.0574 0.084 Uiso 1 1 calc R A .
C12 C 0.4584(3) 1.0177(3) 0.1513(2) 0.0675(8) Uani 1 1 d . A .
H12A H 0.4500 1.0896 0.1152 0.081 Uiso 1 1 calc R . .
C13 C 0.4267(2) 1.0147(2) 0.2374(2) 0.0546(6) Uani 1 1 d . . .
H13A H 0.3964 1.0830 0.2597 0.066 Uiso 1 1 calc R A .
C14 C 0.44096(17) 0.9073(2) 0.29038(17) 0.0415(5) Uani 1 1 d . A .
N1 N 0.40905(15) 0.88247(17) 0.37578(14) 0.0424(4) Uani 1 1 d . . .
H1A H 0.3676 0.9279 0.4014 0.051 Uiso 1 1 calc R A .
C15 C 0.45741(17) 0.76693(19) 0.41476(16) 0.0382(5) Uani 1 1 d . A .
C16 C 0.56371(18) 0.7868(2) 0.49720(16) 0.0415(5) Uani 1 1 d . . .
O1 O 0.60936(16) 0.88317(17) 0.51445(15) 0.0611(5) Uani 1 1 d . A .
O2 O 0.59868(15) 0.68414(16) 0.54270(14) 0.0566(5) Uani 1 1 d . A .
C17 C 0.7051(3) 0.6874(3) 0.6145(2) 0.0740(9) Uani 1 1 d . . .
H17A H 0.7243 0.6070 0.6399 0.111 Uiso 1 1 calc R A .
H17B H 0.7007 0.7409 0.6673 0.111 Uiso 1 1 calc R . .
H17C H 0.7609 0.7165 0.5839 0.111 Uiso 1 1 calc R . .
C18 C 0.3711(2) 0.6977(2) 0.45401(19) 0.0466(5) Uani 1 1 d . . .
O3 O 0.3205(2) 0.6123(2) 0.4179(2) 0.0972(9) Uani 1 1 d . A .
O4 O 0.35844(18) 0.75260(19) 0.53405(14) 0.0649(5) Uani 1 1 d . A .
C19 C 0.2727(3) 0.7049(4) 0.5764(3) 0.0856(11) Uani 1 1 d . . .
H19A H 0.2893 0.7259 0.6448 0.128 Uiso 1 1 calc R A .
H19B H 0.2696 0.6180 0.5695 0.128 Uiso 1 1 calc R . .
H19C H 0.2023 0.7393 0.5430 0.128 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.5(3) . . ?
C6 C1 Br1 119.4(2) . . ?
C2 C1 Br1 118.0(3) . . ?
C6 C1 Cl1' 121.0(3) . . ?
C2 C1 Cl1' 116.3(3) . . ?
Br1 C1 Cl1' 7.6(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C4 C5 C6 123.5(3) . . ?
C4 C5 Cl1 118.1(3) . . ?
C6 C5 Cl1 118.3(2) . . ?
C4 C5 Br1' 117.6(3) . . ?
C6 C5 Br1' 118.8(2) . . ?
Cl1 C5 Br1' 1.2(3) . . ?
C1 C6 C5 115.4(2) . . ?
C1 C6 C7 123.8(2) . . ?
C5 C6 C7 120.8(2) . . ?
C8 C7 C6 124.3(2) . . ?
C8 C7 H7A 117.9 . . ?
C6 C7 H7A 117.9 . . ?
C7 C8 C9 130.7(2) . . ?
C7 C8 C15 124.4(2) . . ?
C9 C8 C15 104.81(17) . . ?
C10 C9 C14 119.5(2) . . ?
C10 C9 C8 132.2(2) . . ?
C14 C9 C8 108.26(19) . . ?
C11 C10 C9 118.6(3) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
C13 C14 N1 127.6(2) . . ?
C13 C14 C9 121.2(2) . . ?
N1 C14 C9 111.1(2) . . ?
C14 N1 C15 108.48(17) . . ?
C14 N1 H1A 125.8 . . ?
C15 N1 H1A 125.8 . . ?
N1 C15 C18 108.04(17) . . ?
N1 C15 C8 104.51(17) . . ?
C18 C15 C8 115.49(18) . . ?
N1 C15 C16 110.82(18) . . ?
C18 C15 C16 110.30(18) . . ?
C8 C15 C16 107.54(17) . . ?
O1 C16 O2 125.4(2) . . ?
O1 C16 C15 123.5(2) . . ?
O2 C16 C15 111.12(19) . . ?
C16 O2 C17 116.7(2) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 124.5(2) . . ?
O3 C18 C15 126.3(2) . . ?
O4 C18 C15 109.1(2) . . ?
C18 O4 C19 116.5(2) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.846(3) . ?
Cl1' C1 1.892(7) . ?
C1 C6 1.383(4) . ?
C1 C2 1.387(4) . ?
C2 C3 1.374(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(4) . ?
C5 Cl1 1.785(4) . ?
C5 Br1' 1.802(5) . ?
C6 C7 1.486(3) . ?
C7 C8 1.325(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.460(3) . ?
C8 C15 1.532(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.400(3) . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H13A 0.9300 . ?
C14 N1 1.385(3) . ?
N1 C15 1.452(3) . ?
N1 H1A 0.8600 . ?
C15 C18 1.530(3) . ?
C15 C16 1.537(3) . ?
C16 O1 1.197(3) . ?
C16 O2 1.315(3) . ?
O2 C17 1.448(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O3 1.172(3) . ?
C18 O4 1.322(3) . ?
O4 C19 1.447(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.86 2.75 3.332(3) 126.7 2
N1 H1A Cl1' 0.86 2.76 3.295(7) 122.0 2
N1 H1A O1 0.86 2.37 3.042(3) 135.1 3_676
C17 H17A O3 0.96 2.56 3.329(4) 137.3 3_666
C19 H19B Br1' 0.96 3.10 3.964(6) 151.2 3_666
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(5) . . . . ?
Br1 C1 C2 C3 176.7(3) . . . . ?
Cl1' C1 C2 C3 -175.0(3) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 Cl1 -178.5(3) . . . . ?
C3 C4 C5 Br1' -179.8(3) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
Br1 C1 C6 C5 -177.9(2) . . . . ?
Cl1' C1 C6 C5 173.5(3) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
Br1 C1 C6 C7 3.9(4) . . . . ?
Cl1' C1 C6 C7 -4.7(4) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
Cl1 C5 C6 C1 -179.8(2) . . . . ?
Br1' C5 C6 C1 -178.5(3) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
Cl1 C5 C6 C7 -1.6(4) . . . . ?
Br1' C5 C6 C7 -0.3(4) . . . . ?
C1 C6 C7 C8 -100.9(3) . . . . ?
C5 C6 C7 C8 81.0(4) . . . . ?
C6 C7 C8 C9 5.5(4) . . . . ?
C6 C7 C8 C15 -170.7(2) . . . . ?
C7 C8 C9 C10 -2.8(4) . . . . ?
C15 C8 C9 C10 174.0(3) . . . . ?
C7 C8 C9 C14 175.7(2) . . . . ?
C15 C8 C9 C14 -7.5(2) . . . . ?
C14 C9 C10 C11 1.2(4) . . . . ?
C8 C9 C10 C11 179.6(3) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 N1 -176.1(3) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C10 C9 C14 C13 -1.3(4) . . . . ?
C8 C9 C14 C13 180.0(2) . . . . ?
C10 C9 C14 N1 175.7(2) . . . . ?
C8 C9 C14 N1 -3.1(3) . . . . ?
C13 C14 N1 C15 -170.2(2) . . . . ?
C9 C14 N1 C15 13.1(2) . . . . ?
C14 N1 C15 C18 -140.48(19) . . . . ?
C14 N1 C15 C8 -17.0(2) . . . . ?
C14 N1 C15 C16 98.6(2) . . . . ?
C7 C8 C15 N1 -168.2(2) . . . . ?
C9 C8 C15 N1 14.7(2) . . . . ?
C7 C8 C15 C18 -49.7(3) . . . . ?
C9 C8 C15 C18 133.3(2) . . . . ?
C7 C8 C15 C16 74.0(3) . . . . ?
C9 C8 C15 C16 -103.12(19) . . . . ?
N1 C15 C16 O1 -11.7(3) . . . . ?
C18 C15 C16 O1 -131.3(2) . . . . ?
C8 C15 C16 O1 102.0(3) . . . . ?
N1 C15 C16 O2 170.53(18) . . . . ?
C18 C15 C16 O2 50.9(2) . . . . ?
C8 C15 C16 O2 -75.8(2) . . . . ?
O1 C16 O2 C17 -4.6(4) . . . . ?
C15 C16 O2 C17 173.1(2) . . . . ?
N1 C15 C18 O3 107.3(3) . . . . ?
C8 C15 C18 O3 -9.3(4) . . . . ?
C16 C15 C18 O3 -131.4(3) . . . . ?
N1 C15 C18 O4 -70.0(2) . . . . ?
C8 C15 C18 O4 173.4(2) . . . . ?
C16 C15 C18 O4 51.2(3) . . . . ?
O3 C18 O4 C19 -2.4(5) . . . . ?
C15 C18 O4 C19 175.0(3) . . . . ?
